There are several things to fear money loss on a bad investment, government involvement in RE, bad tenants that cost time and money, hidden maintenance issues and/or land issues and the list can go on.Today, I don't fear money loss or tenants,  the big unknown is how much the government wants to get involved in either taxes or landlord/tenant issues.

However, you'll minimal capex/maintenance/vacancy and the overall return after 5 years could be very strong. 

Now I agree the 4 will cash flow better than one will but I also look at it from risk of 4 properties will have higher maintenance costs and lower priced properties tend not to appreciate as well as a higher value assetI am also in it for long game and managing one is easier than 4

@Angelo Llamas Even if your rental property breaks even, you should still claim allowable tax deductions like maintenance, travel, insurance, property taxes, and depreciation.

This would include making the listings, setting pricing, finding tenants, managing maintenance requests, and offering deal analysis to investors.

For example, let’s say someone sets an annual goal of cash-flowing $120k ($10k/month) a year in passive income, and then sets a quarterly milestone of acquiring 20 units.

If an investor invested in every one of our 100 + deals since 2015 they’d have an annualized return of 12.4% .  

The plan is to put the rentals in SCH E of our joint return and file with TurboTax-We live in Florida-Leases under my wife's name, Airbnb app under my name, dedicated bank account for all rentals activity in the name of both-We have umbrella policy for liability protection for the rentals-We leverage some contractors (for example cleaning lady for the Airbnbs or lawn maintenance guy) that we pay >$600 for their services in a year and they are not our employees.

And even if they do, they can change that at a monthly BOD meeting.Plus, since you are going to have to hire out the 1) Property Mgmt, 2) Repairs and maintenance, and 3) cleaning, your profit margin is going to be very slim, particualry in a condo (which will have a much leaner net profit than a basic house.Not trying to be a downer, but I'd suggest looking at another avenue for REI. 

But my question is that if we consider other operating costs like maintenance, capital expenditure, vacancy, etc then this property won't cash flow, so is this a good deal?